On December 6th of 2020 around 11AM, Jack messaged Vanessa on Tinder to ask how many boxes of Cheezits she could eat in one sitting. Vanessa replied stating that she would prefer Goldfish instead which led to several debates about the legitimacy of snack options and how viable it was to consume so much in one sitting. After a steady stream of conversation, they had their first FaceTime call on December 7th where they decided to have FaceTime "study dates" each day leading up to their first in-person date. It was on December 11th at Crystal Ridge Winery where they had their first date over a glass of Sauvignon Blanc discussing Salem Witch Trials, Stephen King, and their graduate programs. They arrived at the Winery around 5PM and stayed until the owners closed down the Winery around 9PM. They were so bewitched by each other that they met again for a hike on the 13th and again on the 16th when they decided to make it official. Soon after, Jack went on holiday break to Maine and they communicated each night through FaceTime calls beginning after dinner until 3AM. In short, they have been inseparable since December 6th 2020 and have enjoyed every second of each other's company.

The day began much like any other Sunday where Jack chauffeured Vanessa to all her favorite stores so the shop-a-holic could get her weekly fix. But first, Starbucks where they picked up their ammunition for the day: two Venti Strawberry Açaí refreshers with lemonade. Their first stop was Vanessa's favorite yarn store, Gather Here in Cambridge, to gather supplies for a sweater project she made up as an excuse to buy the yarn (all my knitters know what's up). Then, they made their way over to the Prudential Center where Vanessa acquired the rest of her usual Sunday treats at Sephora and Madewell, with a special stop at Gucci. She grew suspicious when Jack was unusually insistent on making it to their 2:30 reservation at FiorItaly on time. FiorItaly has been a staple in their relationship as it is the location of all of their anniversary dinners and where they choose to celebrate all of their special occasions together over a bowl of gnocchi sorrentina for Jack and fusilli al ragu irpino for Vanessa. It was after appetizers that Jack got down on one knee and proposed. Both of them were so nervous, neither of them really remember what happened, but they're both so happy it did.